{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane

• ChemBase编号: 69483
• 分子式: C44H32P2
• 平均质量: 622.672402
• 单一同位素质量: 622.19792428
• SMILES: c1(c(ccc2ccccc12)P(c1ccccc1)c1ccccc1)c1c(ccc2ccccc12)P(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1ccccc1)c1ccccc1)cccc2)c1ccccc1
• InChI: InChI=1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H
• InChIKey: MUALRAIOVNYAIW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: {1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane
• IUPAC传统名: {1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane; binap
• 别名: (R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘; (±)-2,2′-双(二苯基膦)-1,1′-联萘; 2,2′-双(二苯基膦)-1,1′-联萘; (±)-2,2′-双(二苯基膦)-1,1′-联萘; (+/-)-2,2'-双(二苯基膦基)-1,1'-联萘; (S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘; (R)-(+)-(1,1′-联萘-2,2′-二基)双(二苯膦); (R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘; (S)-(-)-1,1′-联萘-2,2'-双二苯膦; (S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘; (S)-(-)-2,2'-Bis(双二苯基磷)-1,1'-双萘; (R)-(+)-2,2'-联(二苯基膦基)-1,1'-联萘; (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (±)-BINAP; [1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine]; (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; 1,1'-[(1R)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine; (+)-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine]; (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (R)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene; (R)-BINAP; 1,1'-[(1S)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine; (1S)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine]; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (S)-BINAP; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (+/-)-BINAP; (+/-)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine); (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; rac-BINAP; (+/-)-2,2'-Bis(diphenylphosphino)-[1,1']-binaphthyl 98%; (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (R)-(+)-BINAP; (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine); (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl; (R)-BINAP; (S)-(-)-BINAP; (S)-(-)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine); (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl; (S)-BINAP; BINAP; BINAP; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

登记号

• CAS号: 98327-87-8; 76189-55-4; 76189-56-5
• EC号: None
• MDL号: MFCD00010805
• Beilstein号: 5321443; 4914063; 5321444
• 默克索引号: 141223
• PubChem SID: 24871738; 24850475; 162035209; 24857815; 24848870; 24848869; 24857814
• PubChem CID: 634876
• Chemspider ID: 551072
• 维基百科标题: BINAP

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 11.8554
• LogD (pH = 7.4): 11.8554
• Log P: 11.8554
• 摩尔折射率: 195.2244 cm^3
• 极化性: 80.66715 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Benzene; Chloroform; organic solvents
• 外观: Beige Solid; colorless solid; Off-White Solid
• 熔点: 223-225°C; 228-230°C; 238-240 °C(lit.); 238-242 °C (dec.); 239-241 °C(lit.); 239-241 °C (R); 238-240 °C (S); 239-241°C; 281-285°C; 283-286 °C(lit.); 283-286°C
• 比旋光度: [α]19/D +233°, c = 0.3 in toluene; [α]19/D -233°, c = 0.3 in toluene; [α]20/D +222°, c = 0.5% in benzene; [α]20/D +239±5°, c = 0.3% in toluene; [α]20/D -222, c = 0.5 in benzene; [α]20/D -239±5°, c = 0.3% in toluene; +230 (c=0.3 in toluene); -230 (c=0.3 in toluene)
• 作为配体的用途: Acylations; Arylations; Buchwald-Hartwig Cross Coupling Reaction; C-C Bond Formation; Decarboxylations; Stille Coupling

安全信息

• 保存条件: Amber Vial, Refrigerator
• 保存注意事项: Air Sensitive; IRRITANT; Irritant/Air Sensitive/Light Sensitive/Store under Argon
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-37
• TSCA收录: false; 否
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280G-P305+P351+P338
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98.0% (HPLC); 95+%; 97%; 98%
• 级别: puriss.
• 光学纯度: ee: 99% (HPLC); enantiomeric ratio: ≥99.5:0.5 (HPLC)
• 线性分子式: [(C6H5)2PC10H6-]2
• Empirical Formula (Hill Notation): C44H32P2

详细说明

Apollo Scientific Ltd - OR18264

Racemic mixture

Sigma Aldrich - 693057

包装
100, 500 mg in glass bottle
Legal Information
与 Takasago 联合销售，仅供研究使用。
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

Sigma Aldrich - 295825

包装
1, 5 g in glass bottle
250 mg in glass bottle
Application
2,2′-双(二苯基膦)-1,1′-联萘及其铑和钌衍生物可作为高选择性均相催化剂，用于芳基酮、1β-酮酸酯2和 α-氨基酮的还原反应。3也可用于烯烃的不对称氢化4和氢甲酰化反应、5不对称 Heck 反应6和烯丙基的不对称异构化反应。7,8 用于钯催化不对称串联 Heck 反应的配体，这种碳负离子捕获过程可合成三环倍半萜烯。也可用于钌催化的 α,β-不饱和酸的不对称氢化反应。
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

Sigma Aldrich - 295817

包装
1, 5 g in glass bottle
250 mg in glass bottle
Application
过渡金属催化不对称反应（包括氢化1和二甲硅烷基化）的有效配体。22,2′-双(二苯基膦)-1,1′-联萘及其铑和钌衍生物可作为高选择性均相催化剂，用于芳基酮、3β-酮酸酯4和 α-氨基酮的还原反应。5也可用于烯烃的不对称氢化6和氢甲酰化反应、7不对称 Heck 反应8和烯丙基的不对称异构化反应。9,10 其 Ag(I) 络合物可用于催化三氯乙酸链烯酯和醛之间的不对称羟醛反应。11其 Ag(I) 络合物也可用于催化偶氮化合物的不对称非均相 Diels-Alder 反应。12

Sigma Aldrich - 693065

包装
100, 500 mg in glass bottle
Legal Information
与 Takasago 联合销售，仅供研究使用。
Application
Takasago Ligands and Complexes for Asymmetric Reactions

Sigma Aldrich - 481084

Application
钯催化芳基胺偶联反应的配体，用于制备去甲基硫代秋水仙碱。1可与 Cu(II) 联合使用催化芳基磺酰胺加成反应生成苯乙烯和烯烃。2亦可用于钯催化的三联吡啶胺化反应。3
General description
外消旋型 BINAP。4
包装
5, 25, 100 g in glass bottle

Sigma Aldrich - 14798

Application
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation1
• Syntehsis of organophophine oxides as anittumor agents2
• SN2 halogenation of hydroxy groups3
• Synthesis of BINAP complexes4,5
• Studies of conformational flexibility of BINAP chelates6

Sigma Aldrich - 14797

Other Notes
手性阻旋异构双膦；铑和钌络合物可用于不对称氢化和异构化反应1,2,3；制备 BINAP-二羧酸钌络合物4

Toronto Research Chemicals - B386850

Chiral ligand for metal mediated asymmetric catalysis.

Toronto Research Chemicals - B386851

Chiral ligand for metal mediated asymmetric catalysis.

参考文献

• Ito, H., et al.: Nat. Chem., 2, 972 (2010)
• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2010)
• Inui, Y., et al.: Chem. Pharm. Bull., 57, 1158 (2009)
• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2009)
• For use in the Ru-catalyzed homogeneous enantioselective reduction of ketones to secondary alcohols, see: J. Am. Chem. Soc., 117, 2675, 10417 (1995); Org. Synth., 77, 1 (1999).
• The combination with Tris(dibenzylideneacetone)dipalladium(0), 12760, catalyzes the asymmetric arylation of ketone enolates with aryl bromides: J. Am. Chem. Soc., 120, 1918 (1998).
• See also previous entry.
• Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of ɑ-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral enamines: J. Chem. Soc., Chem. Commun., 600 (1982); Synthesis, 665 (1991). Asymmetric hydrogenation of ?-keto esters is achieved with a Ru based catalyst: J. Org. Chem., 57, 6691 (1992). For preparation of a cycloocta-1,5-diene Rh complex and use in enantioselective hydrogenation reaction, see: Org. Synth. Coll., 8, 183 (1993). For a review of the use of Ru BINAP complexes in asymmetric hydrogenation, see: Acta Chem. Scand., 50, 380 (1996).
• Reviews: BINAP catalysis: Acc. Chem. Res., 23, 345 (1990); binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); advances in biaryl-type biphosphne ligands: Tetrahedron, 61, 5405 (2005).